diff --git a/src/anthropic/_files.py b/src/anthropic/_files.py
index f2a6f94e..5bd0cb07 100644
--- a/src/anthropic/_files.py
+++ b/src/anthropic/_files.py
@@ -25,16 +25,14 @@ def is_base64_file_input(obj: object) -> TypeGuard[Base64FileInput]:
 
 
 def is_file_content(obj: object) -> TypeGuard[FileContent]:
-    return (
-        isinstance(obj, bytes) or isinstance(obj, tuple) or isinstance(obj, io.IOBase) or isinstance(obj, os.PathLike)
-    )
+    return isinstance(obj, bytes) or isinstance(obj, io.IOBase) or isinstance(obj, os.PathLike)
 
 
 def assert_is_file_content(obj: object, *, key: str | None = None) -> None:
     if not is_file_content(obj):
         prefix = f"Expected entry at `{key}`" if key is not None else f"Expected file input `{obj!r}`"
         raise RuntimeError(
-            f"{prefix} to be bytes, an io.IOBase instance, PathLike or a tuple but received {type(obj)} instead. See https://github.com/anthropics/anthropic-sdk-python/tree/main#file-uploads"
+            f"{prefix} to be bytes, an io.IOBase instance, or a PathLike but received {type(obj)} instead. See https://github.com/anthropics/anthropic-sdk-python/tree/main#file-uploads"
         ) from None
 
 
diff --git a/tests/test_files.py b/tests/test_files.py
index 4b118fe0..ead9e279 100644
--- a/tests/test_files.py
+++ b/tests/test_files.py
@@ -42,6 +42,17 @@ async def test_async_tuple_input() -> None:
     assert result == IsList(IsTuple("file", IsTuple("README.md", IsBytes())))
 
 
+def test_pathlike_in_tuple() -> None:
+    result = to_httpx_files({"file": ("custom_name.txt", readme_path, "text/plain")})
+    assert result == IsDict({"file": IsTuple("custom_name.txt", IsBytes(), "text/plain")})
+
+
+@pytest.mark.asyncio
+async def test_async_pathlike_in_tuple() -> None:
+    result = await async_to_httpx_files({"file": ("custom_name.txt", readme_path, "text/plain")})
+    assert result == IsDict({"file": IsTuple("custom_name.txt", IsBytes(), "text/plain")})
+
+
 def test_string_not_allowed() -> None:
     with pytest.raises(TypeError, match="Expected file types input to be a FileContent type or to be a tuple"):
         to_httpx_files(